Diethyl Ether → HCID 59165676, compound

HRID 1442534Notes

Reaction equation

HRID 1442534 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](=O)([O-])[O-].[K+].[K+].CI.C(OCC)C>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6088142-Chloro-5-(methylsulfanyl)benzoic acid

Product 1

HCID 59165676HCID 59165676, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-methylsulfanylbenzoic acid (20.2 g, 100 mmol) in N,N-dimethylformamide (200 ml) were added potassium carbonate (15.2 g, 110 mmol) and methyl iodide (6.8 ml, 110 mmol). After stirring at room temperature for 3 hr, diethyl ether (300 ml) was added. The organic layer was washed successively with water (200 ml×3) and saturated brine (200 ml), and dried over magnesium sulfate. Filtration and concentration gave methyl 2-chloro-5-methylsulfanylbenzoate (18.5 g, yield 86%).

Workup

  1. washThe organic layer was washed successively with water (200 ml×3) and saturated brine (200 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-987619b15dbd47e3996bd5119eafa7e0
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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